Fashion Hats

Fashion hats are the instant outfit upgrade you didn’t know you needed—until now. Whether you’re topping off a casual look or adding a dose of drama to your next night out, these styles are all about attitude and versatility. From brunch dates to beach escapes, fashion hats have a way of pulling everything together and making it look intentional. So go ahead, play with proportions, experiment with textures, and let your hat do the talking. Your crown, your rules.

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Windsor Kangol Faux Fur Trim Trapper Hat in Black

$84.90

A black wool-blend trapper hat featuring plush faux fur trim, ear flaps, and signature Kangol embroidery.

Windsor Cold Girl Classic Faux Fur Bucket Hat in Black

$22.90

A cozy black faux fur bucket hat that adds a luxe, stylish touch to any cold-weather look.

Windsor Countryside Chic Buckle Strap Cowboy Hat in Black

$25.90

A black cowboy hat featuring a structured top, curved brim, and an etched buckle strap for western flair.

Windsor Cold Girl Classic Faux Fur Hat in Beige

$25.90

A plush beige faux fur ushanka hat that adds vintage ski-glam style to any winter outfit.

Windsor Cool Girl Cozy Faux Fur Bucket Hat in White

$18.90

A plush white faux fur bucket hat with a soft lining for cozy, stylish everyday wear.

Cold Girl Era Faux Fur Trapper Hat in Ivory

$32.90

A chic ivory faux fur trapper hat featuring cozy ear flaps and an adjustable buckle strap.

City Cozy Tweed Cabby Hat in Ivory

$16.90

A structured ivory cabby hat crafted from textured tweed with a short curved brim and sewn-in lining.

Windsor Kangol Faux Fur Shearling Bucket Hat in Black

$79.90

A cozy black faux fur shearling bucket hat featuring a fleece-lined flap and signature embroidered logo.

Caffeinated And Cute Snapback Hat in Brown

$16.90

A brown snapback hat featuring embroidered “more espresso less depresso” text and an adjustable closure.

Windsor Kangol Corduroy Bucket Hat in Denim

$64.90

A denim blue corduroy bucket hat with classic Kangol logo embroidery and soft cotton construction.

Windsor Kangol Zebra Print Faux Fur Bucket Hat in Olive

$79.90

A plush olive green faux fur bucket hat featuring a bold zebra print and iconic embroidered logo.

Glam In The City Rhinestone Bow Cabbie Hat in Black-2

$16.90

A chic black cabbie hat featuring a rhinestone bow and faux leather brim for standout style.

Windsor Chilly Season Faux Fur Bucket Hat in Ivory-2

$18.90

An ultra-plush ivory faux fur bucket hat with a short brim and cozy woven lining.

Cool Girl Classic Faux Wool Cabby Hat in Beige

$16.90

A structured beige cabby hat crafted from soft faux wool for a polished, effortlessly styled look.

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Windsor Sorry I'm Late, I Stopped For Coffee Baseball Cap in Brown

$12.90

(3)

The perfect baseball cap for all coffee lovers! This adorable hat features an embroidered script reading, "sorry I'm late, I stopped for coffee," and includes a back adjustable strap with a metal buckle. Fit & FeaturesClassic baseball cap design, Round top, Curved brim, Embroidered script reading, "sorry I'm late, I stopped for coffee", Back adjustable strap with metal buckle, Stylish looks perfect for video calls, virtual meetings, happy hours, e-dates, and remote work from home. Free Shipping on All Orders Over $75. | Windsor Sorry I'm Late, I Stopped For Coffee Baseball Cap in Brown

Windsor Cold Girl Classic Faux Fur Bucket Hat in Black

$22.90

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Fuzzy, fabulous, and unapologetically extra. This faux fur bucket hat brings that cozy-luxe vibe to any outfit—perfect for layering up, heading out, or just serving “don’t mess with my winter aesthetic” energy. Fit & FeaturesPlush faux fur exterior, Adjustable inner strings for a snug fit, Classic bucket hat silhouette, Stylish looks perfect for video calls, virtual meetings, happy hours, e-dates, and remote work from home. Free Shipping on All Orders Over $75. | Windsor Cold Girl Classic Faux Fur Bucket Hat in Black

Off Duty Faux Leather Cabby Hat in Black

$18.90

(1)

Serving effortless cool with zero effort—this faux leather cabby hat pulls your whole look together in seconds. Perfect for when you want that model-off-duty vibe without even trying. Fit & FeaturesFaux leather material, Round top, seam accents, button detail, Short curved brim, Woven lined interior, Interior adjustable strings, How To Style For Spooky Season:Pair with a sleek bodysuit and skirt for a fab DIY Halloween look! Stylish looks perfect for video calls, virtual meetings, happy hours, e-dates, and remote work from home. Free Shipping on All Orders Over $75. | Windsor Off Duty Faux Leather Cabby Hat in Black

Windsor Countryside Chic Buckle Strap Cowboy Hat in Black

$25.90

(1)

Enter your western era and look countryside chic in this cowboy hat detailed with an etched buckle strap. Fit & FeaturesStructured top, Curved brim, Thin band, etched buckle, Stylish looks perfect for video calls, virtual meetings, happy hours, e-dates, and remote work from home. Free Shipping on All Orders Over $75. | Windsor Countryside Chic Buckle Strap Cowboy Hat in Black

Windsor Low Key Cool LA Baseball Cap in White

$15.90

(1)

Repping the city never looked this effortless. This LA embroidered baseball cap is the laid-back staple you’ll throw on with everything from streetwear fits to off-duty looks. Fit & FeaturesClassic baseball cap silhouette, Structured curved brim, LA embroidered detail on front, Adjustable back strap for a custom fit, Stylish looks perfect for video calls, virtual meetings, happy hours, e-dates, and remote work from home. Free Shipping on All Orders Over $75. | Windsor Low Key Cool LA Baseball Cap in White

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Windsor Autumn Stroll Corduroy Baseball Cap in Brown

$6.97 $14.90
53% off

(1)

Laidback but make it luxe—this corduroy baseball cap brings cozy texture and fall-girl vibes to your off-duty fits, perfect for pumpkin patches, PSL runs, and downtown strolls. Fit & FeaturesWide curved brim, Classic baseball cap silhouette, Adjustable back strap, Corduroy material, Stylish looks perfect for video calls, virtual meetings, happy hours, e-dates, and remote work from home. Free Shipping on All Orders Over $75. | Windsor Autumn Stroll Corduroy Baseball Cap in Brown

Windsor Cold Girl Classic Faux Fur Hat in Beige

$25.90

Meet your winter style flex. This faux fur ushanka hat keeps you extra warm while serving major vintage ski-glam energy—soft, plush, and ready to make every cold-weather outfit look effortlessly luxe. Fit & FeaturesUltra-soft faux fur exterior, Classic ushanka silhouette, Quilted woven lining, Stylish looks perfect for video calls, virtual meetings, happy hours, e-dates, and remote work from home. Free Shipping on All Orders Over $75. | Windsor Cold Girl Classic Faux Fur Hat in Beige

Windsor Gloria Cap Sleeve Tie Back Mermaid Formal Dress in Navy Blue

$69.90

(1)

The Gloria formal dress is your effortlessly elegant plus-one, designed in a mermaid silhouette with a bold open tie back that makes every head turn! Fit & Features:Smooth knit fabric with stretch, stretchy knit lining, Square neckline, padded bra cups, Cap sleeves, Open tie back design, lower zipper and hook-eye closure, Mermaid silhouette, Floor-length hem, Runs true to size, Where to Wear:Weddings, black tie galas, formal parties and events, engagement parties, rehearsal dinner, fancy date nights, nights at the theatre, school dances Stylish looks perfect for video calls, virtual meetings, happy hours, e-dates, and remote work from home. Free Shipping on All Orders Over $75. | Windsor Gloria Cap Sleeve Tie Back Mermaid Formal Dress in Navy Blue | Size: XS | Knit Fabric

Windsor Cool Girl Cozy Faux Fur Bucket Hat in White

$18.90

Equal parts cozy and cool, this faux fur bucket hat turns any outfit into a moment. The plush texture and effortless shape make it your go-to for chilly coffee runs and everyday styling. Fit & FeaturesBucket hat silhouette, Ultra-soft faux fur material, Soft lining, Stylish looks perfect for video calls, virtual meetings, happy hours, e-dates, and remote work from home. Free Shipping on All Orders Over $75. | Windsor Cool Girl Cozy Faux Fur Bucket Hat in White

Cold Girl Era Faux Fur Trapper Hat in Ivory

$32.90

Snow-day vibes, but make it chic. This faux fur trapper hat brings warmth and attitude with a plush texture and cozy ear flaps that make bundling up actually feel like a style moment. Fit & FeaturesSoft faux fur exterior and lining, Trapper silhouette with ear flaps, Adjustable buckle strap, Stylish looks perfect for video calls, virtual meetings, happy hours, e-dates, and remote work from home. Free Shipping on All Orders Over $75. | Windsor Cold Girl Era Faux Fur Trapper Hat in Ivory

Fashion Hats

If your closet feels like it’s missing that one piece to pull everything together, let’s talk about hats—the unsung heroes of personal style. Whether you’re braving the chill of January winds, chasing a little extra confidence, or just looking for a way to make your everyday outfits feel instantly elevated, a well-chosen hat is your shortcut to standing out (even when you’re bundled up). Winter is prime time to experiment: think cozy beanies for those early-morning coffee runs, felt fedoras that sharpen up your favorite wool coat, or wide-brim styles that turn a simple sweater-and-jeans combo into a full-on vibe. Hats aren’t just for warmth—they’re for attitude, for mood-shifting, and for those “I woke up like this” moments that actually took a little planning. If you’re gifting, hats are that rare find that feels both personal and practical—easy to size, endlessly versatile, and always a conversation starter. Picture your best friend unwrapping a chic Windsor hat that instantly becomes her new signature, or your sister leveling up her winter wardrobe with a playful beret that makes every outfit feel a little more Parisian. The right hat says you know her style—and you know she’s ready to own it.

When it comes to choosing the perfect hat, it’s all about matching your energy to the day ahead. Maybe you’re heading out for a weekend brunch and want something casual-cool, or maybe you’re dressing up for a night out and need a statement piece that turns heads the second you walk in. Windsor hats are designed to flex with your plans—mixing textures, silhouettes, and details that let you dial up (or down) the drama. If you love a little structure, reach for a classic wool fedora to add polish to your winter staples. More into laid-back looks? A slouchy beanie or bucket hat has you covered, literally and stylistically. Don’t forget about those in-between moments: a simple baseball cap can take you from gym to errands without missing a beat, while a newsboy cap brings a retro twist to your favorite oversized blazer. If you’re building a collection, think about color and material—neutrals go with everything, but a pop of bold color or unexpected texture can be the thing that makes your look feel fresh. And if you’re still not sure where to start, or you want something you can throw on with anything, check out our edit of Casual Hats for fuss-free options that work every day of the week.

The magic of a great hat is in the way it transforms not just your outfit, but your whole outlook. There’s a certain confidence that comes from topping off your look with something a little unexpected—a Windsor hat that signals you’re not afraid to play, to experiment, or to turn a few heads on your way to wherever the day takes you. Hats are for everyone—the friend who’s always ahead of the trend, the sister who’s building her signature style, the mom who wants to keep things practical but never boring, and yes, even you, whether you’re a longtime hat devotee or just hat-curious. They’re the perfect accessory for those “nothing to wear” mornings, the secret weapon for last-minute plans, and the finishing touch that makes your winter wardrobe feel intentional and new. So go ahead, give yourself permission to try something different—because with Windsor hats, there’s always room for a little more personality, a little more warmth, and a lot more fun in your everyday style.

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